scholarly journals Electrochemical Organic Synthesis of Electron-Rich Biaryl Scaffolds: An Update

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6968
Author(s):  
Fabrizio Medici ◽  
Simonetta Resta ◽  
Alessandra Puglisi ◽  
Sergio Rossi ◽  
Laura Raimondi ◽  
...  
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Cross Coupling ◽  
Therapeutic Agents ◽  
The Other ◽  
Present Review ◽  
Single Class ◽  
Efficient Alternative ◽  
Privileged Class

Biaryl scaffolds are widely spread in biologically important natural products, in numerous therapeutic agents, but they are also considered a privileged class of ligands and (organo)catalysts; therefore, the development of efficient alternative methodologies to prepare such compounds is always attracting much attention. The present review discusses the organic electrosynthesis of biaryls starting from phenols, anilines, naphthols, and naphthylamines. The most significant examples of the works reported in the last decade are presented and classified according to the single class of molecules: after the introduction, the first three sections relate to the reactions of phenols, naphthols, and anilines, respectively; the other two sections refer to cross-coupling and miscellaneous reactions.

Application of Palladium-Catalyzed Cross-Coupling Reactions in Organic Synthesis

2020 ◽  
Vol 16 (8) ◽  
pp. 1105-1142 ◽  
Author(s):  
Shalu Sain ◽  
Sonika Jain ◽  
Manish Srivastava ◽  
Rajendra Vishwakarma ◽  
Jaya Dwivedi
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Present Review ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

: Palladium-catalyzed cross-coupling reactions have gained a continuously growing interest of synthetic organic chemists. The present review gives a brief account of applications of the palladium-catalyzed cross-coupling reactions in comprehensive synthesis, viz., the Heck, Stille, Suzuki–Miyaura, Negishi, Sonogashira, Buchwald–Hartwig, Ullmann and the Oxidative, decarboxylative cross-coupling reactions, with particular emphasis on the synthesis of heterocyclic compounds.

Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications

2019 ◽  
Author(s):  
Yu Kawamata ◽  
Julien Vantourout ◽  
David P. Hickey ◽  
Peng Bai ◽  
Longrui Chen ◽  
...  
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Second Generation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Catalytic Systems ◽  
Full Disclosure ◽  
Aryl Amination ◽  
Mechanistic Understanding

<div> <div> <div> <p>C–N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles, including complex examples on oligopeptides, medicinally-relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations as well as procedures for both batch and flow scale-ups (100 gram) are also described. </p> </div> </div> </div>

scholarly journals Recent developments on ultrasound-assisted organic synthesis in aqueous medium

2017 ◽  
Vol 82 (7-8) ◽  
pp. 755-790 ◽  
Author(s):  
Bubun Banerjee
Keyword(s):  
Green Chemistry ◽  
Aqueous Medium ◽  
Organic Synthesis ◽  
Ultrasonic Irradiation ◽  
The Other ◽  
Present Review ◽  
Recent Past ◽  
Environmentally Sustainable ◽  
Recent Developments ◽  
Ultrasound Assisted

In the recent past, a number of methods were reported on the application of ultrasound in organic reactions for the synthesis of diverse organic scaffolds. On the other hand, as far as green chemistry is concerned, water is the safest of all solvents. Thus, a ?strong collaboration? between ultrasonic irradiation and aqueous medium holds the key to the development of an environmentally sustainable protocol. The present review summarizes the latest developments in ultrasound-assisted and water-mediated organic synthesis reported to date.

Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications

2019 ◽  
Author(s):  
Yu Kawamata ◽  
Julien Vantourout ◽  
David P. Hickey ◽  
Peng Bai ◽  
Longrui Chen ◽  
...  
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Second Generation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Catalytic Systems ◽  
Full Disclosure ◽  
Aryl Amination ◽  
Mechanistic Understanding

<div> <div> <div> <p>C–N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles, including complex examples on oligopeptides, medicinally-relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations as well as procedures for both batch and flow scale-ups (100 gram) are also described. </p> </div> </div> </div>

scholarly journals Catalyst Controlled Regiodivergent C-H Alkynylation of Thiophenes

2020 ◽  
Author(s):  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Bioactive Molecules ◽  
Reaction Conditions ◽  
Common Procedure ◽  
Broad Scope ◽  
Palladium Catalyzed

Alkynes are highly attractive motifs in organic synthesis due to their presence in natural products and bioactive molecules as well as their versatility in a plethora of subsequent transformations. A common procedure to insert alkynes into hetero(arenes), such as the thiophenes studied herein, consists of a halogenation followed by a Sonogashira cross-coupling. The regioselectivity of this approach depends entirely on the halogenation step. Similarly, direct alkynylations of thiophenes have been described that follow the same regioselectivity patterns. Herein we report the development of a palladium catalyzed C–H activation/alkynylation of thiophenes. The method is applicable to a broad range of thiophene substrates. For 3-substituted substrates where controlling the regioselectivity between the C2 and C5 position is particularly challenging, two sets of reaction conditions enable a regiodivergent reaction, giving access to each regioisomer selectively. Both protocols use the thiophene as limiting reagent and show a broad scope, rendering our method suitable for late-stage modification.

scholarly journals Catalyst Controlled Regiodivergent C-H Alkynylation of Thiophenes

2020 ◽  
Author(s):  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Bioactive Molecules ◽  
Reaction Conditions ◽  
Common Procedure ◽  
Broad Scope ◽  
Palladium Catalyzed

Alkynes are highly attractive motifs in organic synthesis due to their presence in natural products and bioactive molecules as well as their versatility in a plethora of subsequent transformations. A common procedure to insert alkynes into hetero(arenes), such as the thiophenes studied herein, consists of a halogenation followed by a Sonogashira cross-coupling. The regioselectivity of this approach depends entirely on the halogenation step. Similarly, direct alkynylations of thiophenes have been described that follow the same regioselectivity patterns. Herein we report the development of a palladium catalyzed C–H activation/alkynylation of thiophenes. The method is applicable to a broad range of thiophene substrates. For 3-substituted substrates where controlling the regioselectivity between the C2 and C5 position is particularly challenging, two sets of reaction conditions enable a regiodivergent reaction, giving access to each regioisomer selectively. Both protocols use the thiophene as limiting reagent and show a broad scope, rendering our method suitable for late-stage modification.

scholarly journals Natural Bioactive Cinnamoyltyramine Alkylamides and Co-Metabolites

Biomolecules ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1765
Author(s):  
Antonio Evidente ◽  
Marco Masi
Keyword(s):  
Natural Products ◽  
Biological Activities ◽  
Antioxidant Properties ◽  
Carbon Skeleton ◽  
The Other ◽  
Present Review ◽  
Natural Sources ◽  
Plant Kingdom ◽  
Structural Variability ◽  
Plant Families

Natural products are a vital source for agriculture, medicine, cosmetic and other fields. Among them alkylamides are a broad and expanding group found in at least 33 plant families. Frequently, they possess a simple carbon skeleton architecture but show broad structural variability and important properties such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal and antioxidant properties, amongst others. Despite to these several and promising biological activities, up to today, only two reviews have been published on natural alkylamides. One focuses on their potential pharmacology application and their distribution in the plant kingdom and the other one on the bioactive alkylamides specifically found in Annona spp. The present review is focused on the plant bioactive cinnamoyltyramine alkylamides, which are subject of several works reported in the literature. Furthermore, the co-metabolites isolated from the same natural sources and their biological activities are also reported.

Phytosome Drug Delivery of Natural Products: A Promising Technique for Enhancing Bioavailability

2017 ◽  
Vol 7 (03) ◽  
Author(s):  
Rani Anjana ◽  
Kumar Sunil ◽  
Sharma Hitender ◽  
Khar R. K.
Keyword(s):  
Drug Delivery ◽  
Natural Products ◽  
Plant Extract ◽  
Herbal Extract ◽  
Present Review ◽  
Absorption Profile ◽  
Promising Technique ◽  
Characterization Techniques ◽  
Advanced Form

The phytosome technology was developed by Indena markedly enhancing the bioavailability of selected phytomedicines, by incorporating phospholipids into standardized plant extract, which improve their absorption and utilization. Phytosome are advanced form of herbal extract that shows better absorption profile than conventional herbal extract. The present review focus on the preparation and characterization techniques of phytosomes, merits and various landmarks in the field of phytosomes.

A Comprehensive Review on the Therapeutic Versatility of Imidazo [2,1-b]thiazoles

2020 ◽  
Vol 27 (40) ◽  
pp. 6864-6887 ◽  
Author(s):  
Mohd Adil Shareef ◽  
Irfan Khan ◽  
Bathini Nagendra Babu ◽  
Ahmed Kamal
Keyword(s):  
Literature Review ◽  
Medicinal Chemistry ◽  
Therapeutic Agents ◽  
Present Review ◽  
Thiazole Derivatives ◽  
Pharmacological Activities ◽  
Comprehensive Review ◽  
Derivatives Of

Background:: Imidazo[2,1-b]thiazole, a well-known fused five-membered hetrocycle is one of the most promising and versatile moieties in the area of medicinal chemistry. Derivatives of imidazo[2,1-b]thiazole have been investigated for the development of new derivatives that exhibit diverse pharmacological activities. This fused heterocycle is also a part of a number of therapeutic agents. Objective:: To review the extensive pharmacological activities of imidazo[2,1-b]thiazole derivatives and the new molecules developed between 2000-2018 and their usefulness. Method:: Thorough literature review of all relevant papers and patents was conducted. Conclusion:: The present review, covering a number of aspects, is expected to provide useful insights in the design of imidazo[2,1-b]thiazole-based compounds and would inspire the medicinal chemists for a comprehensive and target-oriented information to achieve a major breakthrough in the development of clinically viable candidates.

p-Sulfonic acid calix[n]arene catalyzed synthesis of bioactive heterocycles: A review

2020 ◽  
Vol 24 ◽  
Author(s):  
Bubun Banerjee ◽  
Gurpreet Kaur ◽  
Navdeep Kaur
Keyword(s):  
Supramolecular Chemistry ◽  
Sulfonic Acid ◽  
Catalytic Efficiency ◽  
The Other ◽  
Reaction Conditions ◽  
Metal Free ◽  
Bioactive Scaffolds ◽  
Wide Range ◽  
Efficient Alternative ◽  
Bioactive Heterocycles

: Metal-free organocatalysts are becoming an important tool for the sustainable developments of various bioactive heterocycles. On the other hand, during last two decades, calix[n]arenes have been gaining considerable attention due to their wide range of applicability in the field of supramolecular chemistry. Recently, sulfonic acid functionalized calix[n] arenes are being employed as an efficient alternative catalyst for the synthesis of various bioactive scaffolds. In this review we have summarized the catalytic efficiency of p-sulfonic acid calix[n]arenes for the synthesis of diverse biologically promising scaffolds under various reaction conditions. There is no such review available in the literature showing the catalytic applicability of p-sulfonic acid calix[n]arenes. Therefore, we strongly believe that this review will surely attract those researchers who are interested about this fascinating organocatalyst.

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